CA2080907A1 - Enzymatic synthesis of soluble phosphatides from phospholipids - Google Patents
Enzymatic synthesis of soluble phosphatides from phospholipidsInfo
- Publication number
- CA2080907A1 CA2080907A1 CA002080907A CA2080907A CA2080907A1 CA 2080907 A1 CA2080907 A1 CA 2080907A1 CA 002080907 A CA002080907 A CA 002080907A CA 2080907 A CA2080907 A CA 2080907A CA 2080907 A1 CA2080907 A1 CA 2080907A1
- Authority
- CA
- Canada
- Prior art keywords
- salt
- monovalent
- enzyme
- divalent
- phosphatidyl ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000003904 phospholipids Chemical class 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 230000002255 enzymatic effect Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 4
- 125000002091 cationic group Chemical group 0.000 abstract 3
- -1 phosphatidyl ester Chemical class 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 102000004190 Enzymes Human genes 0.000 abstract 2
- 108090000790 Enzymes Proteins 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 150000001450 anions Chemical group 0.000 abstract 1
- 239000008366 buffered solution Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 238000006911 enzymatic reaction Methods 0.000 abstract 1
- 150000002632 lipids Chemical class 0.000 abstract 1
- 239000002502 liposome Substances 0.000 abstract 1
- 238000004810 partition chromatography Methods 0.000 abstract 1
- 150000003138 primary alcohols Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/106—Adducts, complexes, salts of phosphatides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6481—Phosphoglycerides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P9/00—Preparation of organic compounds containing a metal or atom other than H, N, C, O, S or halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
Abstract
A method of preparing a soluble monovalent salt of a phosphatidyl ester which comprises reacting a phospholipid with a primary alcohol in the presence of an enzyme catalyst in a divalent cationic buffered solution and a water immiscible non-ether solvent that does not inactivate the enzyme, to form a divalent cationic salt of the phosphatidyl ester, and suspending the product in the presence of a stoichiometric amount of a monovalent cationic salt whose anion forms an insoluble salt with the divalent cation. The use of Centrifugal Partition Chromatography facilitates the enzyme reaction. The monovalent salt is preferably an ammonium/sodium mixed salt.
Phosphatidyl ester salts prepared by processes disclosed herein are useful products for making liposomes and lipid-based complexes.
Phosphatidyl ester salts prepared by processes disclosed herein are useful products for making liposomes and lipid-based complexes.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51328590A | 1990-04-17 | 1990-04-17 | |
| US513,285 | 1990-04-17 | ||
| PCT/US1991/002608 WO1991016444A1 (en) | 1990-04-17 | 1991-04-16 | Enzymatic synthesis of soluble phosphatides from phospholipids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2080907A1 true CA2080907A1 (en) | 1991-10-18 |
| CA2080907C CA2080907C (en) | 2001-08-14 |
Family
ID=24042616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002080907A Expired - Lifetime CA2080907C (en) | 1990-04-17 | 1991-04-16 | Enzymatic synthesis of soluble phosphatides from phospholipids |
Country Status (15)
| Country | Link |
|---|---|
| EP (2) | EP0727491B1 (en) |
| JP (1) | JP3169132B2 (en) |
| AT (2) | ATE181747T1 (en) |
| AU (1) | AU646458B2 (en) |
| CA (1) | CA2080907C (en) |
| DE (2) | DE69123145T2 (en) |
| DK (2) | DK0727491T3 (en) |
| ES (2) | ES2094811T3 (en) |
| GR (2) | GR3022375T3 (en) |
| HU (1) | HU212928B (en) |
| IE (1) | IE911264A1 (en) |
| NZ (1) | NZ237845A (en) |
| PT (1) | PT97391B (en) |
| WO (1) | WO1991016444A1 (en) |
| ZA (1) | ZA912877B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060165606A1 (en) | 1997-09-29 | 2006-07-27 | Nektar Therapeutics | Pulmonary delivery particles comprising water insoluble or crystalline active agents |
| US7871598B1 (en) | 2000-05-10 | 2011-01-18 | Novartis Ag | Stable metal ion-lipid powdered pharmaceutical compositions for drug delivery and methods of use |
| DE10142014B4 (en) | 2001-08-28 | 2004-11-11 | Degussa Bioactives Deutschland Gmbh & Co. Kg | Process for the preparation of phosphatidylserine |
| CA2468958C (en) | 2001-12-19 | 2012-07-03 | Nektar Therapeutics | Pulmonary delivery of aminoglycosides |
| US6878532B1 (en) | 2003-04-28 | 2005-04-12 | Sioux Biochemical, Inc. | Method of producing phosphatidylserine |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1900959A1 (en) * | 1969-01-09 | 1970-08-27 | Unilever Nv | Process for the production of plant phosphatides with universal emulsifying power |
| US4235792A (en) * | 1977-04-14 | 1980-11-25 | The Governing Council Of The University Of Toronto | Immunological materials |
| SU831129A1 (en) * | 1979-07-24 | 1981-05-23 | Дальневосточный Государственный Уни-Верситет | Method of obtaining phosphatidylglycerin |
| US4485045A (en) * | 1981-07-06 | 1984-11-27 | Research Corporation | Synthetic phosphatidyl cholines useful in forming liposomes |
| US4587055A (en) * | 1982-05-26 | 1986-05-06 | Research Corporation | Polymerized vesicles and compounds for their preparation |
| US4783402A (en) * | 1983-04-11 | 1988-11-08 | Meito Sangyo Kabushiki Kaisha | Production of primary or secondary alcohol derivatives of phospholipids by the enzymatic technique |
| JPS62205788A (en) * | 1986-03-05 | 1987-09-10 | Shoichi Shimizu | Production of phosphatidylglycerol or derivative thereof |
| IL87449A0 (en) * | 1987-08-14 | 1989-01-31 | Liposome Technology Inc | Preparation of phosphatidylglycerol |
| US4997761A (en) * | 1987-10-06 | 1991-03-05 | Houston Biotechnology Incorporated | Phosphatidyl treatment of viral disease |
| DE69011739T2 (en) * | 1989-05-26 | 1995-01-19 | Kao Corp | Process for the preparation of phosphatidic acid. |
-
1991
- 1991-04-16 AT AT96100985T patent/ATE181747T1/en not_active IP Right Cessation
- 1991-04-16 AU AU76995/91A patent/AU646458B2/en not_active Expired
- 1991-04-16 ES ES91908298T patent/ES2094811T3/en not_active Expired - Lifetime
- 1991-04-16 WO PCT/US1991/002608 patent/WO1991016444A1/en active IP Right Grant
- 1991-04-16 CA CA002080907A patent/CA2080907C/en not_active Expired - Lifetime
- 1991-04-16 JP JP50805391A patent/JP3169132B2/en not_active Expired - Lifetime
- 1991-04-16 EP EP96100985A patent/EP0727491B1/en not_active Expired - Lifetime
- 1991-04-16 AT AT91908298T patent/ATE145244T1/en not_active IP Right Cessation
- 1991-04-16 DE DE69123145T patent/DE69123145T2/en not_active Expired - Lifetime
- 1991-04-16 IE IE126491A patent/IE911264A1/en not_active IP Right Cessation
- 1991-04-16 ES ES96100985T patent/ES2132780T3/en not_active Expired - Lifetime
- 1991-04-16 NZ NZ237845A patent/NZ237845A/en unknown
- 1991-04-16 DE DE69131404T patent/DE69131404T2/en not_active Expired - Lifetime
- 1991-04-16 DK DK96100985T patent/DK0727491T3/en active
- 1991-04-16 EP EP91908298A patent/EP0528834B1/en not_active Expired - Lifetime
- 1991-04-16 HU HU9203258A patent/HU212928B/en unknown
- 1991-04-16 DK DK91908298.2T patent/DK0528834T3/en active
- 1991-04-17 ZA ZA912877A patent/ZA912877B/en unknown
- 1991-04-17 PT PT97391A patent/PT97391B/en not_active IP Right Cessation
-
1997
- 1997-01-23 GR GR970400109T patent/GR3022375T3/en unknown
-
1999
- 1999-08-23 GR GR990402138T patent/GR3031059T3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU212928B (en) | 1996-12-30 |
| HU9203258D0 (en) | 1993-01-28 |
| ATE145244T1 (en) | 1996-11-15 |
| AU7699591A (en) | 1991-11-11 |
| ES2094811T3 (en) | 1997-02-01 |
| EP0528834A1 (en) | 1993-03-03 |
| IE911264A1 (en) | 1991-10-23 |
| EP0727491A1 (en) | 1996-08-21 |
| JP3169132B2 (en) | 2001-05-21 |
| GR3022375T3 (en) | 1997-04-30 |
| WO1991016444A1 (en) | 1991-10-31 |
| NZ237845A (en) | 1993-06-25 |
| EP0727491B1 (en) | 1999-06-30 |
| CA2080907C (en) | 2001-08-14 |
| PT97391A (en) | 1991-12-31 |
| DE69131404T2 (en) | 1999-11-25 |
| PT97391B (en) | 1999-04-30 |
| EP0528834A4 (en) | 1993-06-02 |
| GR3031059T3 (en) | 1999-12-31 |
| EP0528834B1 (en) | 1996-11-13 |
| DE69123145T2 (en) | 1997-06-12 |
| DE69123145D1 (en) | 1996-12-19 |
| DK0727491T3 (en) | 1999-11-22 |
| AU646458B2 (en) | 1994-02-24 |
| ES2132780T3 (en) | 1999-08-16 |
| DE69131404D1 (en) | 1999-08-05 |
| ZA912877B (en) | 1992-12-30 |
| ATE181747T1 (en) | 1999-07-15 |
| HUT63198A (en) | 1993-07-28 |
| DK0528834T3 (en) | 1997-04-07 |
| JPH05509222A (en) | 1993-12-22 |
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| OH | II zyxwvutsrqponml |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20110416 |